


Best Laid Plans

by starsdontsleep



Category: Pirates of the Caribbean (Movies)
Genre: Alternate Universe - Canon Divergence, Attraction, Jealousy, Kissing, Love, M/M, Pining, Prostitution
Language: English
Status: Completed
Published: 2020-08-30
Updated: 2020-08-30
Packaged: 2021-03-06 17:01:49
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,273
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26192359
Author URL: https://archiveofourown.org/users/starsdontsleep/pseuds/starsdontsleep
Summary: Will wants Jack, but believes the pirate won’t want an inexperienced lover. He goes looking for a male whore, but it doesn’t work out as planned when Jack sees him enter the brothel.Post CotBP, disregards other movies.
Relationships: Jack Sparrow/Will Turner, Past Elizabeth Swann/Will Turner
Comments: 2
Kudos: 182





	Best Laid Plans

**Author's Note:**

> I ended up unable to get them out of my head. So, I wrote something else tonight. Still working out their voices, hopefully it's alright.

Will had never been interested in prostitutes.

He wasn’t a prude or a eunuch (as Jack so often called him). He just didn’t like the idea of paying someone for their company. He had also spent his life loving and admiring Elizabeth. The temptations of the working women of Port Royale had never interested him. They would have only tarnished his pure and unwavering feelings for Elizabeth.

But, after meeting Jack Sparrow and saving Elizabeth, he’d learned that his feelings for her couldn’t stand up to the light of day - let alone survive a marriage to someone he had pined for from afar, but never truly knew.

They’d both agreed to break their engagement and remain friends.

Three months later, Will had left Port Royale chasing after whispers and rumours of the Black Pearl. He hadn’t understood why, at the time. But nearly a year at sea with Jack had made it abundantly clear.

He’d been ensnared at twelve by the beautiful woman who’d saved him. 

And he’d been ensnared as a young man by the glittering pirate who’d showed him how to live.

Loving Elizabeth from afar hadn’t prepared him for loving Jack up close.

Not, that he’d admitted his attraction or affection to the pirate. It had taken him months to even acknowledge it to himself and even longer to accept it. 

But he had seen many of the men on the Pearl take comfort and pleasure from each other. Jack had all but rubbed his nose in it within his first few months. He’d taken Will to a brothel with a few members of the crew. He had refused company, but Jack and many of the others hadn’t.

He’d seen some crew members buy male whores that night. He’d even seen Jack flirt with one of the men, letting him sit in the pirate’s lap. Will hadn’t been prepared for it then. He’d been shocked and a little horrified. (He’d also been jealous, although he hadn’t known that at the time.)

Afterwards, Jack had told him it was no more of a sin then pillaging, plundering and living life as a cutthroat pirate. Jack had watched him carefully, but Will had heard of sailors who took other men. Even naval officers. It wasn’t displayed so openly in polite society, but Will supposed pirates didn’t care much for laws and polite society.

Will hadn’t treated the crew any differently and Jack had never brought it up again.

Mostly, Will had ignored the habits of the Pearl’s crew, but as his own feelings had developed for his captain, he’d started paying greater attention.

Jack predominately took women, but occasionally, he took men. He didn’t visit the brothels as often as the other members of the crew. Sometimes, he would spend the whole shore leave with Will. Drinking, planning their next voyage, showing him the port town and telling him ridiculous tall tales.

Will didn’t like seeing Jack leave with a whore, but despite his jealousy and pain, seeing him leave with a man infused within him a raw sense of hope. Because, if Jack took male lovers, the pirate might be willing to bed _him_. Will was certain he had seen Jack’s eyes wander over his body more than once. Jack found him attractive. Will just needed to prove he was worth taking to bed.

He was certain that a virgin wouldn’t be interesting to Jack. He could have his pick of pretty, talented prostitutes. Will needed to be, if not as talented as them, at least aware of the basics of sex with a man.

It was what found Will stepping inside one of Tortuga’s many brothels. He had never taken a whore, but if he wanted to make his proposition sound good to Jack, he needed to be more than a blushing virgin.

Unfortunately, once he got there, a flaw in his plan became abundantly clear.

He didn’t know how to entice one of them. Normally, a man sitting alone with a tankard of rum would garner a flock of attention. But he had a reputation around the working men and women of Tortuga. They knew that William Turner would always be polite, but would never, _ever_ accept any of them.

They’d long given up wasting precious time on him that could be spent on someone else.

And Will didn’t know how to fix that. Or rather, he didn’t know how to approach one of them and _ask_ for them to pleasure him. His face turned pink at the thought and he ended up sullenly staring into his rum.

It was as he was sitting there, debating what to do, that someone landed heavily in the seat beside him. He jerked up, his hand immediately reaching for a dagger before the man spoke and his voice registered, “Not a place I’d be expecting to find you, Will.”

Will relaxed even as he shot Jack a small glare. He had _not_ wanted to run into the pirate, but fate it seemed, wasn’t being generous to him tonight. Jack was in his customary jacket and hat. His kohl-rimmed eyes looked even darker in the dim tavern and his own tankard of rum was clasped in one tanned, relaxed hand.

“I’m allowed to get a drink, Jack,” Will said.

He could already feel the warmth from Jack’s body as he sat too close. Jack _always_ sat too close. He had no respect for personal boundaries and Will had long stopped being flustered by that and instead, he grew dependant on it. He found himself yearning for a clap on the back, an arm around his shoulders or their bodies pressed together at a table as they conversed.

“Oh, yer are,” Jack agreed, nodding his head. “But, not exactly the _place_ I’d be expecting you. You’re aware you picked a place where _drinking_ ain’t the main priority, aren’t ya?” He frowned and tilted his head, his eyes looking around Will’s empty table. “Or maybe you ain’t too worried.” He grinned. “Could think you _were_ a eunuch the way they don’t touch yer for any number of shillings.”

Will rolled his eyes and looked away from Jack. Normally, getting privacy in Tortuga was something he was grateful for, now, having Jack point it out, made him want to grind his teeth. The pirate didn’t know he’d struck a nerve, but Will was on edge about going through with his plan, let alone by having the pirate he desired at his side, pointing out his failings.

“Now, if you only let dear ol’ Jack help you out, I could get us a nice little group to pick from. Help loosen you up, it would.”

It wasn’t the first time Jack had made the offer, in fact, he made it routinely. He always shook his head and chuckled when Will refused. He’d smile and tell Will he couldn’t _possibly_ be a pirate with such a bleak attitude towards rum and pleasure. They’d get into an argument and Jack would end up leaning against his side extoling the virtues of sex until Will shifted the topic and they ended up back at the Pearl drinking in Jack’s cabin.

But tonight, Will _didn’t_ say no. Instead, he did something _incredibly_ stupid. 

He turned to Jack, caught his gaze and said, “Alright.”

Jack blinked and he went completely still. It was possibly the only time he’d ever seen Jack so surprised.

“What was that, Will? I don’t think I heard you right.”

“I said, alright. Go pick some and bring them to the table and I’ll take one to bed.”

Jack blinked again and although Will’s heart was pounding and a small voice in the back of his head was calling him _so, incredibly stupid_ , another part of him was taking pleasure in actually surprising Jack. 

He decided to push it even further. To lay down, if not his offer, then at least his reception to more than just women.

“You know what, Jack. If I’m doing this tonight, we might as well make it interesting. Bring me some men too.”

“Men,” Jack repeated.

Will held his captain’s gaze and didn’t flinch. “ _Men_. You’ve told me before I need a good _buggering_.”

At the time, Jack had been cursing up a storm. Will had gotten hurt and was refusing to lay down and was instead trying to help get the ship back in order. Jack had shouted all kinds of things at him. That one in particular had stuck in his mind. Mostly, because it had made him picture _Jack_ buggering him and that had distracted him so much that he’d let Jack sit him down, check him over and make him stop working.

It was one more part of why he was here in the first place.

When Jack finally reacted to his statement, it was to smile and slap Will hard on the back. He laughed loudly and took a swig of rum. He shook his head, still chuckling.

“If I didn’t know you better mate, I’d have believed ya. I think that calls for another round.” 

He shifted as if getting ready to stand and search out more rum. Will grabbed Jack’s arm and kept him in his seat.

“I’m not lying, Jack,” Will insisted.

Jack frowned, looking puzzled. Will abruptly knew that Jack wouldn’t believe him without proof. Instead, they would have one of their arguments, like two bulls locking horns until the night was over and they were walking back to the Pearl, squabbling companionably. Unlike the usual exasperated fondness it would cause, tonight it ignited his stubbornness and before he knew what he was doing, Will stood. He looked at the startled captain.

“If you won’t bring them here. I’ll have to find them myself.”

Will picked up his tankard and threw the rest back in a single swallow. He was grateful for the high alcohol tolerance he’d gained sailing with a crew of heavy drinkers. He barely flinched and walked with steady legs towards a group of whores. He hardly made it a few steps before he felt Jack’s hands on his arm.

“Now, Will,” Jack said. “Let’s not do anything stupid.”

Will whirled on him, feeling annoyed suddenly.

“I thought I was taking my _Captain’s_ advice. You’ve wanted me to gain a good fucking for months now, Jack. Why shouldn’t I do what every other member of this crew does? There are plenty of men and women here who would fill the position.”

“I’ll giv’ ya ha’f price,” a rather pretty brunette called from nearby, having obviously heard their conversation. “Ain’t all of ‘em so pretty as ‘urner.”

She thrust her breasts forward and smiled with rum-stained teeth. Laughter and cheers erupted around the small area. Will’s cheeks immediately flushed, especially when he noticed at least five other prostitutes looking at him with ample interest. 

When one of the men Jack had taken to bed sidled up and touched his arm, Will jerked to look at him. The man leaned forward as if to whisper in his ear, but a low growl erupted from his other side. Will was yanked away until he stumbled into Jack’s chest.

The man’s eyes widened and he scurried away without another word. When Will glanced at Jack, he saw the pirate’s hand had gone to his cutlass. He was still scowling after the man. Will felt indignation flood him. 

It wasn’t fair that he had to deal with Jack teasing and encouraging him to utilise brothels, only to now have him sabotage his attempts to do so. Will was too angry to think. He yanked out of Jack’s hold, only surprise allowing him to do it. Will turned on his heel and strode out of the brothel. He needed to calm down or he was going to do something he’d regret.

_Like punch Jack. Or tell him to take their place._

The thought sent a flush of heat through him. His cheeks went pink even as arousal flooded his body. He focused on the heavy fall of his feet and his long strides rather than the tightening of his breeches.

“Will!” Jack shouted, running along behind him.

Will ignored him.

“Oi! Don’t be gettin’ sore you couldn’ make yo’r point,” Jack said, catching up to him. “Ain’t nothing good comin’ from it. You ain’t the whorin’ type. S-not to be ashamed of.”

Will whirled on him. It made Jack pull up short, but their faces were still inches from one another they were so close.

“I was about to _be_ the ‘whoring type,” Will snarled. “I went into that brothel for a _reason_ , Jack.”

Nor for the first time tonight, Jack looked completely thrown. But, this time, he recovered quickly. Something Will couldn’t pinpoint flickered through his eyes. It shuttered them in a way Will wasn’t used to.

“You ain’t the kind, luv,” Jack said, his voice oddly quiet. “Think you’d regret it. Never would’a pushed if I’d known you were gonna take it.”

The words struck something inside Will and had him glancing away. Jack was _right_ and Will knew it. Perhaps it was silly and idealistic of him, but he believed that sex should be… special, _intimate_. He’d waited on the hopes of sharing the moment with Elizabeth on their wedding night.

Then, in the months after the ending of their courtship, he hadn’t thought about bedding anyone. When he’d fallen for Jack, he’d immediately wanted more than a quick fuck in the captain’s cabin, but he’d known expecting anything else was laughable. He’d still been willing to settle for it. To throw away what he wanted for what he could have.

When he felt Jack’s hand on his arm, he glanced down and then up to the captain’s face.

“Why’d you decide all of a sudden, mate?”

Will almost laughed. It seemed so ludicrous. Here was the man he was trying to gain sexual experience for, and Jack was not only _stopping_ him from bedding a whore, but was now enquiring _why_ he wanted said lover in the first place. 

Will didn’t answer, but it didn’t seem to bother Jack. Instead, Jack slid his hand down Will’s arm. He took Will’s hand, making him startle. He then stiffened as Jack’s other hand went to his neck. Will looked up and found his face far too close to Jack’s. He could feel the man’s breath; sweet with rum and a hint of spice. Jack always smelt like some far-off location, mixed with sweat, brine and the faint scent of cannon fire. 

When Jack tugged him backwards, Will haltingly followed until the light of the main street was replaced for the dimness of an alley.

“J-Jack,” he said, his voice hitching in the middle.

“Shh,” Jack murmured. 

He tugged Will again and it ended with Jack’s back against the building’s wall and Will bending over him. He felt frozen. He knew his eyes were wide. Jack had let go of his hand and now Will’s hands hovered in the air, not sure what to do.

Jack’s lips twitched in a faint smile, but only for a moment before he pulled on Will’s neck. At the same moment, Jack tilted up his chin. Their lips came together and Will sucked in a startled gasp. Jack took immediate advantage and pushed his tongue inside Will’s mouth. Will gave a small squeak that quickly turned into a groan. His eyes fell closed and his hands finally moved to capture Jack’s waist. Jack made a noise of approval and his free arm slid around Will’s lower back. He yanked him forward and their pelvises came together. Will groaned again and tilted his head to better kiss Jack.

He’d kissed Elizabeth numerous times during their courtship, but it was nothing like this.

Elizabeth had been tender and chaste, both of them learning what the other liked and how to use their lips. Tongues hadn’t even come into it. Jack kissed how he sailed; with vigour and confidence. He plundered Will’s mouth and left Will light-headed and eager for more. Each scrape of Jack’s facial hair sent a shiver down Will’s spine. 

When they finally parted for breath, Will panted. His forehead rested against Jack’s and he kept his eyes closed. Jack’s breath was equally ragged, but he was the first to compose himself.

“You ain’t to go lookin’ for any more whores, William Turner,” he said, his voice more order than request. 

Will’s eyes opened and he pulled back to better see Jack’s face. He’d rarely seen the pirate look more serious. Will’s heart raced for a new reason and his hands felt clammy against Jack’s waist.

“Why shouldn’t I do that?” Will asked, his voice more composed then he’d expected.

“Because Captain Jack Sparrow doesn’t _share_. Savvy?”

Will’s breath hitched. Jack was possessive, Will knew that. But only about the things he felt were important. Things he claimed as _his_. The Black Pearl. Rum. His hat. There wasn’t a _person_ on that list. At least, not before now.

But, he couldn’t let his hopes sail away from him. 

Wary of giving himself away, Will hedged, “You’re making a lot of assumptions, Jack.”

A smug smile curved Jack’s lips and his fingers slipped into Will’s hair, making him shudder.

“Am I?” Jack enquired. “Seems like you ain’t protesting too much. Seems like maybe you’d be happy letting ol’ Jack taking you to his cabin and,” Jack leaned forward, trailing his mouth over Will’s jaw, “keep you from all those nasty regrets.”

Will swallowed. “And what’s to say _you_ won’t be my regret, Jack?”

Jack paused his slow kisses, but only for a moment.

“Simple, love,” Jack said, pulling back with a smirk. “I’m Captain Jack Sparrow.”

“Jack-” Will protested, frustrated.

Jack pressed two fingers to Will’s lips before he could continue. His eyes, when Will caught them, were unexpectedly warm.

“And,” he said, “I’ll make it good for yer, Will.” Jack traced the curve of his lip, his gaze soon following the path, staring at Will with longing. “Been waitin’ a long while to make it good for yer.” He looked back up. “Ain’t about to make a mess now I got my chance, am I?”

Will knew Jack could be cryptic and deceptive, but looking at him now, Will didn’t think he’d ever seen the pirate be more open or honest. There was promise in his eyes and words.

_Because Captain Jack Sparrow doesn’t **share**._

Will swallowed again. “And how many regrets are you going to protect me from?”

“All of ‘em,” Jack said. Briefly, uncertainty flashed through his eyes and he tightened the fingers in Will’s hair. “Whenever you want me to.” His voice lowered, becoming little more than a whisper. “Cabin’s always open to you, Will.”

It was exactly what he’d wanted to hear, but hadn’t thought was possible. Slowly, Will smiled. 

“If that’s the case, Jack,” Will said, leaning down and daring to pass his lips over Jack’s. “I think we have an accord.” 

He pressed his lips firmer and this time, Jack groaned. His hand, if possible gripped Will tighter. The touch was possessive and filled with coiled desire and anticipation. It sparked the same inside Will until his body was almost trembling.

He _wanted_ Jack, and finally, he would have him.

Breaking the kiss, Will panted. “Take me back to your cabin, Jack.”

Jack grinned. It was his wide, smug, _delighted_ grin. The kind that only appeared when a treasure was in his sights and mere moments from his grasp. It made Will’s heart skip to be the focus of that look.

It seemed his plan had worked out even better than he’d hoped.


End file.
